4-Chloro-3-methoxybenzoic acid → 4-Amino-5-chloro-6-ethoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

HRID 2407815Notes

Reaction equation

HRID 2407815 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:10][CH3:11])[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.ClC1C=CC(C(O)=O)=CC=1OC.Cl.Cl.Cl.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[S:37][C:38]([CH2:41][N:42]2[CH2:47][CH2:46][CH:45]([CH2:48][NH2:49])[CH2:44][CH2:43]2)=[CH:39][N:40]=1>>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:10][CH3:11])[N:5]=[C:4]([C:12]([NH:49][CH2:48][CH:45]2[CH2:46][CH2:47][N:42]([CH2:41][C:38]3[S:37][C:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=4)=[N:40][CH:39]=3)[CH2:43][CH2:44]2)=[O:14])[CH:3]=1

Participants

4

Reactant 3

HCID 20633784-Chloro-3-methoxybenzoic acidHCID 118462894-Amino-5-chloro-6-ethoxypicolinic acidHCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride

Product 1

HCID 585041964-Amino-5-chloro-6-ethoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

Procedure

According to the same procedure described in Example 16 and starting with 4-amino-5-chloro-6-ethoxypicolinic acid (prepared according to the reported preparation in J. Med. Chem. 2006, 49, 4455) instead of 4-chloro-3-methoxybenzoic acid and the compound prepared in Example 214 instead of the compound prepared in Example 9, the title compound having the following physical data was obtained. 1H NMR (DMSO-d6): δ 8.61 (d, J=4.7 Hz, 1H), 8.33 (t, J=6.4 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (td, J=1.7, 7.7 Hz, 2H), 7.78 (s, 1H), 7.47 (ddd, J=1.1, 4.8, 7.5 Hz, 1H), 7.09 (s, 1H), 6.50 (s, 1H), 4.45 (q, J=7.0 Hz, 2H), 3.73 (s, 2H), 3.16 (t, J=6.5 Hz, 2H), 2.85-2.88 (m, 2H), 1.97 (t, J=10.7 Hz, 2H), 1.60-1.63 (m, 2H), 1.50-1.55 (m, 1H), 1.31 (t, J=7.0 Hz, 3H), 1.15-1.24 (m, 2H);

Workup

  1. customprepared
  2. customaccording to the reported preparation in J

Sources & evidence

ORD record
ord-0fb02a6680a84e83ad905b929de3a94b
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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